Consider This: jcp Oxford Shirt, $28

Meet your wardrobe's new workhorse. You can wear these with just about anything—untucked over denim or shorts or tucked into a pair of slim khakis. Roll up the sleeves for a more laid-back look. Stock up on solids first: You need a blue and white one. Then you can branch out to bengal stripes and other colors like seafoam or red. Yes, you can throw these under a suit jacket, but not on formal occasions—the button-down collars place these shirts firmly in the casual category. You can still dress them up a little though.